The ‘Roots’ of reinvention: Meghan Roach on leading an iconic Canadian brand

Catherine Clark: You grew up in a small town in Ontario. Given the big job you have now, what part of that upbringing still shows up in how you lead?

Meghan Roach: Yeah, so I grew up in a small town – Pembroke, which is part of the Ottawa Valley – very close to Ottawa, about an hour and a half northwest. I think the thing about growing up in a small town is that everyone is very close. There are a lot of shared values, and there’s this strong focus on what you contribute to the community.

That sense of hard work, giving back, and recognizing that everything you do has an impact on the place where you live and work – that’s really stayed with me. In my current role, I’m always asking myself: Am I staying true to my values? Am I doing something that helps move the business forward, and also supports my community? That sense of community you get from growing up in a small town has absolutely stayed with me.

Jennifer Stewart: I love that. I’m from Renfrew – not quite as deep in the Ottawa Valley, but I know the feeling. There’s such a humbleness that comes from being raised in a small town. But I want to shift gears a bit. When you were appointed CEO, it was literally weeks before the pandemic hit. What was your first “Oh my gosh” moment as a new CEO during a global crisis?

Meghan Roach: We had a business in China, and our distribution centre was in Wuhan. So we actually saw the pandemic start to unfold earlier than most markets. In February, we began seeing shutdowns in China, and that’s when the first realization hit: we might not be able to get product from any region globally for quite some time. We were asking ourselves – how much inventory do we have? How long can we operate like this?

That was the first knock: understanding that this global event was going to affect us in North America, and quickly. As a global business, we felt the impact right away.

Then came the second big moment. When COVID started hitting Canada, we had to make the incredibly difficult decision to temporarily lay off a large number of employees. I remember sitting there the day we made that call, watching as provinces across the country began declaring states of emergency – starting in the East Coast and moving west.

We initially thought, “Okay, we’ll close stores and begin temporary layoffs in provinces that issue emergency orders,” thinking it would be isolated. But by the end of the day, almost the entire country had followed suit.

I was looking at our employee numbers – about 2,500 people, with roughly 2,000 working in retail – and realized I had to be the one to make that call. It was about getting them to the front of the line for unemployment insurance, protecting their health and safety, and trying to preserve the business.

That’s when it really sank in: I’m the CEO. The buck stops here. Coming from private equity, I was used to making big decisions, but always across a portfolio of companies – so no one decision carried this kind of immediate, deeply personal impact. To be in that position just a few months into the role, wondering whether we’d even have a business in six months… that was a huge weight. But it also clarified what leadership really means.

Catherine Clark: In those early days of the pandemic, with so much uncertainty and being brand new in the role, how did you steady yourself – not just your team, but you personally?

Meghan Roach: I think going back to that small-town upbringing, I felt really grounded in the values I was raised with. There was always this idea that it’s not about what you have – it’s about who you are, what you’re doing, and how you’re doing it. That’s what really matters.

So when I was facing difficult decisions, I often thought, “Can I live with myself after I make this call?” None of the choices were great – they were all hard – but I tried to make the least worst one with the information I had at the time. I wanted to be able to wake up the next day and feel like I’d done the best I could.

As a CEO, there’s also a responsibility to project confidence and calm. Your team takes their cues from you. If you’re scattered or visibly worried, they’ll absorb that. But if you can stay focused, calm, and clear on the direction you need to take, they’ll follow that energy too.

For me, it became less about what I was doing – since, again, all the options were tough – and more about how and why I was doing it. I tried to anchor each decision in my values and principles.

Jennifer Stewart: That calmness is such a superpower. You’ve also spoken before about being underestimated. How have you turned that perception into an advantage rather than letting it hold you back?

Meghan Roach: When I was younger, it bothered me more. I felt like I had to prove myself all the time – walk into a room and immediately say something smart or show that I was accomplished and experienced.

As I’ve grown more comfortable in my role, I’ve actually started using being underestimated to my advantage. It gives me space to listen and learn more. Sometimes people don’t expect much from you, so they focus their attention elsewhere – which gives you a unique vantage point to really observe and assess the situation.

For example, if you’re in a boardroom or a meeting and you’re the only woman, or maybe the most junior person in the room, expectations might be lower. That gives you an opportunity to take a step back, analyze what’s happening, and approach the situation more strategically and thoughtfully.

Catherine Clark: It sounds like your confidence has really evolved over time. Do you still ever walk into a room and think, “Wow, I feel out of place”?

Meghan Roach: I would say I do. But I also know, having done this now for so long, that it’s important not to let that show. And so I think there’s a lot of internal self-talk that you really have to think about. You can get into that room and give yourself five seconds of, “Okay, wow, I’m in this room,” and then you need to flip it around and be like, “Yes, I’m in this room. Why am I here? What’s my goal? What’s my purpose?” And really portray that confidence – but also have it internally and externally.

Because I think people can really read that. When you get into a situation where you feel uncertain about yourself, the effect is often that the situation actually gets worse. Whereas if you come into a situation with a certain amount of confidence and calmness, and you set that level from the start, I think things usually work out better.

So I would say I definitely have those experiences, but I’ve learned a lot more about how to get over them. And maybe an example I’ll give you is that I used to be really afraid of public speaking. I hated it. I got incredibly nervous and I was a terrible public speaker. I’d like to think I’ve gotten a little bit better – maybe I still have some work to do – but one of the things I was always worried about was, “What are people thinking about me when I get out there? Can they tell how nervous I am?”

The more I did it, and the more I saw other people do it, the more I realized that nobody wants to see you fail in that experience. So you really only hurt yourself by being nervous, because everyone else out there wants you to succeed. They’re there to see you for a reason.

Now it’s much easier for me to do public speaking, because I go in thinking, “Okay, take the five minutes of nervousness, put that to the side, and really focus on the fact that nobody else wants you to fail in this situation.” That gave me a different level of confidence, I think.

And the repetitions – having done a couple of things and failed at those things, and then thinking, “Well, I failed… what happened? How bad really was it?” – and then continuing to do that on repeat… I think that gives you a certain level of confidence, too. Which just makes it easier. 

Jennifer Stewart: Meghan, you’re a mom, you’re a partner, you’re a CEO. What does a normal day actually look like for you?

Meghan Roach: I don’t really have any normal days. I wish I did, but unfortunately, especially now – given the changing landscape and the last five and a half years in this role – every day has been a different day.

So I try to have a few things I focus on. I spend a little bit of time with my kids – either seeing them in the morning or the evening, before or after school – so that they have a touchpoint with me at some point during the day.

I try to really focus on working out. Putting fitness into my routine is really important, and it’s become even more important as I get older and as I’ve been in this role longer. It’s just really good stress relief, and it gives you a sense of accomplishment that you can carry with you throughout the day – even if everything else doesn’t go the way you want.

And then, really, it’s flexible. It depends if I have to travel, it depends on what’s going on at work, and where my time and attention need to be. So I spend a lot of my day doing different things, speaking to different people, and finding myself in a variety of situations.

Catherine Clark: Jen and I – part of the reason we work really well together is because we have different approaches to life, and it’s strangely complimentary.

I don’t have a lot of non-negotiables, but I also have slightly older kids, so outside of my professional schedule, I can be a little more flexible with when I respond to emails, etc.

Jen has non-negotiables. Sometimes they drive me crazy, because I’m like, “Girlfriend, I need you to answer!”

Do you have non-negotiables? You’re at the stage where you have younger kids too. Are there non-negotiables that are absolutely fixed in your calendar and help you stay grounded?

Meghan Roach: I don’t have non-negotiables. I don’t have set non-negotiables. I kind of pick and choose mine.

So what I would say is: I don’t often get a chance to go to my kids’ events, but if I decide I’m going to one, then that’s it – I’m not available at that time. I make it very clear that I’m out, I’m doing this one thing, and I try to give it 100% of my focus.

So I don’t have a set schedule of non-negotiables, but every now and then I’ll pick something where I say, “I’m going to do this, I’m not going to be interrupted, and this is a key focus.”

I’d say the biggest non-negotiable I do have is the concept of regular fitness in my routine. I’ve always loved fitness. I’ve always been into it. But I’ve now found that in this role, it’s something I have to do.

So I try to find time to make that happen. I don’t necessarily block a specific time in my calendar every day, but I look at it over a week and make sure I get to the gym a certain number of times. I also try to find something engaging from a fitness perspective.

I’ve learned a lot more about myself – what I can do in terms of flexibility, and how much I can handle. I might say no to more things now than I used to, or I think more deliberately about it. If I’m going to say yes to something, then what’s the knock-on effect?

What’s the impact on the rest of my schedule – on my ability to be a parent, a CEO, a board member? How do I factor in the ripple effect of saying yes to that one thing?

Jennifer Stewart: Meghan, you know this better than any of us, but Roots is such a nostalgic brand for so many people. What’s your strategy for modernizing the brand while protecting what people love and think of when they think about Roots?

Meghan Roach: I think that’s really important – when you have a brand like Roots, or any heritage brand – the fact is, you have to recognize that, especially with a brand like Roots, which is 50 years old, you have customers across all age ranges who’ve had different experiences with it.

And it’s not necessarily my brand – it’s a number of people’s brand, right?

So when you think about it, I actually grew up after the brand was founded. My experience growing up with Roots is different from someone who was there when it launched and grew up with it from day one.

The way we think about modernization is by recognizing that Roots is not just a brand about product – it’s really about emotional connectivity. So the question becomes: how do you think about that emotional connection people have with the brand, and how do you work with it to modernize?

What we’ve been doing over the last five and a half years is moving things slowly. I don’t think you can move quickly with a heritage brand. You have to be considered in the moves you make so that, over time, people notice the shift – but it’s not so drastic that it feels jarring.

By the time you get to your end point, you’ve moved pretty significantly – but people don’t feel like it’s that far, because they’ve been with you on the journey.

If you went to Roots today and walked around the store, what you’d see is: almost all of our products are now made with sustainable materials, which is a huge shift. We’re much more modern in terms of silhouettes. We have fewer logos, different materials, an active collection – things that, five years ago, you wouldn’t have seen at all.

But if you come in today, you’ll think, this feels fresh, this feels modern. And at the same time, it still makes sense in the context of what Roots has always stood for – because we’ve been slowly, intentionally moving in that direction every year.

A little bit more, a little bit more – and now it all feels cohesive from a brand perspective because of that.

Catherine Clark: I had a pair of Roots leather lace-up boots – the ankle-height ones – that I bought in my first year of university after I moved to Toronto. I felt like I had made it, because I had these boots that were the coolest thing ever. What’s one change you made at Roots – whether to the product or the brand – that felt risky, but in the end, really paid off?

Meghan Roach: I think the introduction of activewear was one of those things that felt risky for us, because people didn’t necessarily perceive us as an active brand in that way. People think of us as an outdoor brand; they think about us for the comfort and quality of our materials.

So when we first said, “We’re going to do activewear,” I think people initially asked, “Why would you do that? You’re not one of those big activewear brands.”

But we put it in the context of: we see that our customers are using our products for a variety of use cases. They want us for softness, hand feel, that on-body feel. So we built a collection that was really focused on that – and we’ve had great traction with it.

It wasn’t about becoming just another activewear brand. It was about asking, how are people using active materials in their everyday lives? And how does that relate to Roots?

I knew it was a little riskier. But to your point – going back to your boots – when you talk about them, it’s not just about the boots. It’s the experience. You remember having them, but also where you wore them, what you were doing, how you felt.

I have a similar connection. I have a vintage sweater from the 1980s. I still wear it, and every time I do, I think about wearing it at my cottage. It used to belong to one of my older siblings, and now it’s mine. That nostalgia – that emotional connection – is powerful.

So we think a lot about that dynamic: how do you emotionally connect people to the decisions you’re making and the products you’re launching?

Even with something like activewear, we don’t think about it in a singular way, like I’m just going to run. We think about it in terms of: what are the active activities people are doing together that foster emotional connectivity and a sense of self within a group?

How can the product engage with people in a way that builds that sense of community?

Jennifer Stewart: It’s such a cool opportunity to lead a brand that so many Canadians – and people outside Canada – associate with memories and meaning.

Meghan, if you could give one piece of advice to your 25-year-old self walking into her first room, what would it be?

Meghan Roach: I think I’d go back to something we talked about earlier – the idea that you don’t have to be the smartest person in the room.

You have to take a second to assess the situation. Think about: Why are you there? Why are they there? There’s a lot to learn from others.

When you’re younger, you spend a lot of time focused on when am I going to get there? or how am I going to get there?You’re always thinking about the future, and not enough about where you are now.

Now that I’m older, I spend more time thinking about the present – where I am, where the people I engage with are. I learn a lot just by listening to people who’ve done something interesting with their lives.

I try to understand: How did you get there? What did you do? And it’s funny, because I’m doing this now – at a stage where I’ve already done a few different things – and you might ask, “Why now?” But I wish I had done more of that earlier.

I wish I had asked more questions, listened more, learned more, understood how people achieved what they did – their struggles, the techniques they used, the tools that helped them.

I also wish I had tested and learned more. Tried more. Failed more. Taken more risks.

Because in the end, it’s a very long life. You’ve got a long career ahead of you. Yes, the things you do early in your career are important – but you’ve got a lot of time to grow.

So it’s important to get out there, try things, test things, take risks, and figure out what it is you really want to do.